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FAD’s Hot Picks for Fall Festivals & Apple Picking In and Around Fairfield County
Fall is calling! Cooler days, changing leaves, apple picking, cider donuts, country fairs, pumpkin patches and fall festivals are returning throughout Connecticut and the Hudson Valley.
One of the best things about living in Fairfield County is how many great fall destinations are within an easy drive. You can stay close to home, head toward the Connecticut shoreline or Litchfield Hills, or cross the New York border for a Hudson Valley fall road trip.
Fairfield After Dark has rounded up some of our Hot Picks for Fall 2026. Grab your sweater and start planning!
🍎 FAIRFIELD COUNTY
Blue Jay Orchards — Bethel A local fall favorite for pick-your-own apples, pumpkins, a farm market and those must-have cider donuts.
Silverman’s Farm — Easton Apple picking, pumpkins, a country market and animal farm make Silverman’s an easy family fall outing.
Beardsley’s Cider Mill & Orchard — Shelton Pick apples and stock up on fresh cider, cider donuts, pies and other bakery favorites.
Aki Matsuri Fall Festival — Westport | Sept. 19 Japanese culture takes over Jesup Green with taiko drumming, dancing, martial arts, activities and a marketplace.
Westoberfest — Westport | Oct. 3 Downtown Westport celebrates Oktoberfest with local and regional beer, live music and fall fun.
NICE Festival — Norwalk | Oct. 3 Oyster Shell Park comes alive with international food, music, dance, arts, crafts and cultural performances.
🍏 NEW HAVEN COUNTY
Bishop’s Orchards Fall Festival — Guilford | Through Nov. 1 One of FAD’s biggest fall picks with apple picking, a corn maze, wagon rides, pumpkins, food and seasonal activities.
Rose Orchards — North Branford Apples, pumpkins, corn maze, wagon rides, farm market and creamery make this a full fall afternoon.
Blue Hills Orchard — Wallingford A traditional Connecticut orchard experience with seasonal apple picking and wagon rides.
Guilford Fair — Sept. 18–20 A classic agricultural fair with rides, animals, exhibits, food, crafts and entertainment.
Orange Country Fair — Sept. 19–20 Old-fashioned country-fair fun filled with agriculture, food, entertainment and family activities.
Seymour Pumpkin Festival — Sept. 20 French Memorial Park fills with arts, crafts, food and family activities celebrating fall.
Milford Oktoberfest — Sept. 25–26 Head to Fowler Field for beer, food, music and traditional Oktoberfest festivities.
🍂 LITCHFIELD COUNTY
Averill Farm — Washington Depot Pick apples and pears while enjoying one of the most picturesque old-fashioned farm experiences in the Litchfield Hills.
March Farm — Bethlehem Pick-your-own fruit, a farm market, bakery, animals, corn maze and weekend hayrides.
The Farm — Woodbury | Through Oct. 30 Corn maze, pumpkins, hayrides, sunflowers, music and seasonal farm fun.
Harwinton Fair — Oct. 2–4 Pig races, tractors, animals, bluegrass, food and plenty of old-fashioned country-fair traditions.
Connecticut Garlic & Harvest Festival — Bethlehem | Oct. 10–11 Garlic, harvest foods, vendors and fall festivities take over the Bethlehem Fairgrounds.
🍎 WESTCHESTER COUNTY, NY
Harvest Moon Farm & Orchard — North Salem Apple picking meets fall festival with hayrides, live music, cider donuts, seasonal food and pumpkins.
Outhouse Orchards — North Salem Apples, pumpkins, corn maze, hayrides and cider donuts make this another North Salem favorite.
Stuart’s Fruit Farm — Granite Springs A traditional apple-picking destination with a farm stand, bakery and weekend hayrides.
Wilkens Fruit & Fir Farm — Yorktown Heights Apple picking, farm-market goodies and seasonal treats make Wilkens another Westchester fall tradition.
🍎 PUTNAM COUNTY, NY
Salinger’s Orchard — Brewster No pick-your-own here, but definitely worth a stop for locally grown apples, cider donuts, pies and its Farm Market & Bakery.
🍏 DUTCHESS / RENSSELAER COUNTIES, NY
Fishkill Farms — Hopewell Junction Apple and pumpkin picking, wagon rides, cider donuts, seasonal food and Treasury Cider make this a great Hudson Valley day trip.
Goold Hill Estate – Castleton-on-Hudson Goold Hill Estate is now open, welcoming guests for apple picking, family-friendly farm experiences, live music and events, artisan markets, seasonal treats, locally crafted ciders, and a glimpse at its future Estate wines.
Barton Orchards — Poughquag Go big with apple and pumpkin picking, family attractions, food, entertainment and fall festival weekends.
Meadowbrook Farm — Wappingers Falls A smaller farm experience for apples, pumpkins, cider donuts and seasonal farm-market shopping.
Hudson Valley Wine & Food Festival — Rhinebeck Make it a grown-up fall road trip with regional wines, craft beverages, food and Hudson Valley producers.
🍎🍩 FAD’s Fall Advice: Never Skip the Cider Donuts!
Whether you stay close to home in Fairfield County, head north into the Litchfield Hills or cross the border into New York, there’s plenty of fall fun waiting within an easy road trip.
Remember: Apple varieties, picking conditions, hours and activities can change throughout the season. Check directly with farms and festivals before heading out, especially when pick-your-own apples are the main reason for your visit.
Now grab the family, your friends — or your favorite fall date — and go enjoy autumn!
Keep checking
FairfieldAfterDark.com
for more Fall Happenings, Halloween Events, Fairs, Festivals, Live Music and Things To Do in and around Fairfield County.
